Versatile Synthesis of Multivalent Porphyrin-Peptide Conjugates by Direct Porphyrin Construction on Resin

摘要

Multifunctional porphyrin-peptide conjugates with different propensities for self-assembly into various supramolecular nanoarchitectures play important roles in advanced materials and biomedical research.However,preparing prefunctionalized core porphyrins by traditional low-yielding statistical synthesis and purifying them after peptide ligation through many rounds of HPLC purification is tedious and unsustainable.Herein,we report a novel integrated solid-phase synthetic protocol for the construction of porphyrin moieties from simple aldehydes and dipyrromethanes on resin-bound peptides directly to form mono-,cis/trans-di-,and trivalent porphyrin-peptide conjugates in a highly efficient and controllable manner;moreover,only single final-stage HPLC purification of the products is needed.This efficient strategy enables the rapid,greener,and substrate-controlled diversity-oriented synthesis of multivalent porphyrin-(long)peptide conjugate libraries for multifarious biological and materials applications.